69 - Uncorked at Scale w/CEO of First Batch - Brian Leventhal

Welcome to ⁠Digital Doorways⁠, the podcast where we explore the intersection of brand, growth, leadership, and the strategic decisions that shape modern companies. I’m⁠ Jason Siegel,⁠ founder of ⁠Bluetext⁠. On this show we talk with founders, operators, and marketers about how businesses actually scale — how positioning, experience design, and disciplined execution open the digital doorways that lead to growth, enterprise value, and long-term relevance.Today’s guest has built a business that flips the traditional winery model on its head. ⁠Brian Leventhal ⁠is the co-founder and CEO of ⁠First Batch⁠, the company behind a portfolio of urban winery and event-driven venues including District Winery in Washington, DC, Brooklyn Winery in New York, and Chicago Winery in you guessed it - Chicago.What makes Brian’s story so interesting is the platform he’s built: creating authentic, working wineries while designing a business whose primary economic engine is large-scale events and weddings. It’s a model that blends production, place, and experience — and in the process, has reimagined how a winery business can grow, scale, and translate across multiple major U.S. markets.QUESTIONSUrban wineries weren’t common when you started. What was the original insight that made you believe this concept could work in major cities?When you first launched the business, did you envision building a multi-city platform like First Batch, or did that evolve over time?What did you see in the market that others weren’t seeing yet?Traditional wineries focus primarily on wine production and tasting rooms. You built something very different. How did the idea of combining a winery with a large-scale event venue evolve?Across your venues, weddings and events are the core economic engine. At what point did you realize that would become central to the model?Many event venues feel generic, but your properties feel authentic to the craft of winemaking. How intentional was that balance across the portfolio?What were the hardest decisions in preserving winery authenticity while building an event-driven business at scale?If someone attends an event at one of your venues — whether it’s District Winery, Brooklyn Winery, or Chicago Winery — what experience do you want them to walk away remembering?When you look at the company today, is the product really the wine — or is it the broader experience surrounding it?How important is physical design — architecture, views, and environment — to creating a consistent but locally relevant experience?You’ve successfully expanded into multiple major cities under the First Batch umbrella. What makes the model replicable?What ingredients have to exist in a market for one of your winery concepts to work?When you enter a new city, how do you evaluate whether the concept fits that location?What lessons from your earlier locations made the newer ones stronger?Hospitality businesses are notoriously difficult to scale. What systems or frameworks have you built at the platform level to make expansion possible?When you think about growth, do you view First Batch primarily as a real estate strategy, a brand strategy, or an operational playbook?What does the next phase of expansion look like for the company?Running large-scale events requires incredible operational discipline. What systems have you built across the organization to make that repeatable?What leadership lessons have you learned building a company where every event is essentially a live performance, across multiple markets?Looking five or ten years ahead, what excites you most about the future of First Batch and experiential hospitality more broadly?